7 Biggest Mistakes I’ve Personally Made as a Lifestyle Entrepreneur

By Sean Ogle •  Updated: 06/06/13 •  10 min read

“While one person hesitates because he feels inferior, the other is busy making mistakes and becoming superior.” – Henry C. Link

Earlier this week I shared with you the 7 biggest mistakes I’ve seen beginning lifestyle entrepreneurs make when starting their businesses.  Ever since I posted that I haven’t been able to stop thinking about my own mistakes that I’ve been making.

I’m far from perfect with my business, and there are some mistakes I’ve made that have definitely been haunting me over the last year as I continue to build and scale things over here.

So I guess I figure that if I’m still dwelling on this a couple days later, then you’ll probably get some value out of me getting really open, and just laying it all out there.

So here you go.

These are the 7 biggest mistakes I’m currently making in my business, as well as a little insight into why I’ve made them, and what I’m doing to fix it.

I’m really not necessarily looking for any feedback on this stuff.  I could give you a hundred things I could do for any one of these things, it really comes down to me just making conscious decisions about where I want things to go, and what I’m going to make a priority over the coming months.

1) Not Establishing Relationships with Big Influencers

I’m kind of in this weird middle ground when it comes to entrepreneurship. I have more drive and motivation than many of the people who just want a thousand bucks and a backpack, but I’m not necessarily looking to build a $100 million business either.

There are a few people who I’ve seen really thrive lately by relentlessly pursuing friendships, mentorships, and relationships with people who have had more success than them.

Scott Dinsmore is one who has been particularly impressive.  His site Live Your Legend really hasn’t been around that long, but he’s built friendships with some of the most successful people online, and has truly taken everything they’ve said to heart, and scaled his business quickly.

Dane and Andy of The Foundation have done the same thing, on an even larger, more profitable scale.

Now, I’ve met and know a lot of successful entrepreneurs, but I haven’t gone above and beyond. I haven’t tried to write guest posts on their blogs or worked to create partnerships that have the potential of reaching a much larger audience.

This is a huge missed opportunity, and one of the things I want to change the most over the coming months.

2) Not rounding out my product offerings

This one is a little bit more complicated.  I have three primary products Overcoming the Fear of Uncertainty, Location Rebel Academy, and Hacking the High Life.

Soon they will all be merged into one site, as it truly is the “perfect lifestyle business course”. Overcome your fears to make a major life change, build the online business, live the life you’ve always wanted. It’s awesome and a ton of people have had success with it.

That said, I’ve got a lot of ideas for what’s next but haven’t decided exactly what that’s going to be.  Last year I made the conscious decision to double down on Location Rebel because it has been so successful, and it’s only gotten better.

While no matter what, that will be the core of my business, it’s time to start thinking about what the next big product is, and how it’s going to relate to the existing community.

I’m lucky. I have a big list of subscribers and followers that have proven they will happily buy if I give them a product that truly blows them away with results and value – I could be leveraging that much more than I am, which would help more people, and make me more money in the process.

#3) Poor General Wellness Habits

This is the absolute biggest mistake I’ve made, hands down.

I go in waves when it comes to positive habits and routines.  Lately, I’ve had a schedule that has me traveling quite a bit for short periods at a time – this is a total routine killer for me.

Right now my routine is wake up lateish (7:30-8), drink 2 cups of coffee, work for a few hours, pretend to work for a few mores, and then go out and drink/eat un-healthy food at night.  It’s a good social routine, but terrible overall wellness routine.

I know what I have to do in order to not only perform at my best, but be happy as well. It’s stupid simple: Wake up early, eat healthy, exercise.

Wow, shocker right?

Lately, I’m lucky if I do one of those things on any given day. And it makes such a remarkable difference when I put all of those things together.

When you not only work for yourself, but by yourself, these things carry even more importance.  They can help break up work periods, which makes you more productive. When I’m doing these things I get more done, and thus have more time to do things I like to do (even more important now that the summer weather has shown up here in PDX).

This is applicable for every single person reading this. Are you struggling in your business? Get your shit together when it comes to general wellness, and I promise you it will have a positive impact on your work.

Less time in front of a computer, doesn’t by any means, equate to less output.

4) Too much lifestyle, not enough business

This may be less mistake and more learning process.  In the past I’ve said, when given the opportunity for fun or work, I’ll almost always choose fun. Why? Because that’s one of the primary benefits of this lifestyle.

Lately, however I’ve maybe veered too much towards the lifestyle and not enough the business.

A lot of this falls back on the fact I work by myself and have a terrible case entrepreneur’s ADD.  I have no problem spending 8 hours in front of a computer, the issue is that rarely is even the majority of that time well spent.

So I’ll often “work” for 6 hours and then go out and do fun stuff in the afternoons and evenings.  If I really worked early on, this would be the perfect balance, but I’m not getting enough done during my work times to justify the amount of playing I do when the weather is good.

So is this a mistake? Probably not, I certainly don’t regret any of it.  It’s more a matter of finding ways to be your most productive self, and the real mistake is not devoting more time to figuring out how to be that super productive, focused person thats lying inside of me.

5) Not Optimizing Email/Sales Funnel

My sales funnel for my products are good, but not great.  The biggest problem is that they conflict with each other. If you sign up for both the Location 180 and Location Rebel email lists at similar times, you end up getting more emails from me than you probably should.

This simple fix would do a number on conversions, and while I have a great plan for this that I’m working on, it’s taken much longer to materialize than I initially thought – see mistakes 3 and 4 above.

That said, bear with me, as it is getting closer, and this means a LOT of really useful free material for you.

While I get a lot of compliments on my emails, I’m still not sure I’ve struck the perfect balance between providing truly useful stuff and talking about myself. Sometimes it falls too far to the latter, which I’m not happy with.

The bottom line, is I truly believe email is the most powerful marketing tool we have as lifestyle entrepreneurs.  I generally know what to do, but the implementation hasn’t been as good as it needs to be.

6) Not Failing More

It’s been a little while since I did something that I’d consider an all out failure.  While you never want to fail, when you do, it usually means you’re taking a risk, trying something new, and learning a ton in the process.

I’ve had some projects or services that haven’t gone as well as I’d hoped, but none have been outright failures.  There are some things I’ve thought about doing, but haven’t due to a variety of factors, most of which are based on the fear of failure.

I’ve hammered home the idea that there is only one fear in the world, uncertainty.  In many aspects of my life, I’m able to successfully view it as an asset and take calculated risks.  However, sometimes it’s easier to stay with something that works (to a point), is comfortable, but isn’t necessarily catapulting you forward.

I need more catapulting in my life, even if that does result in the occasional flop.

7) Poor Long Term Planning

Finally we have another one of the really big mistakes: poor long term planning. I’ve been talking about a few BIG initiatives for the last year. Things like a Location Rebel event, full overhaul of all my sites, and more, but because I haven’t committed and haven’t truly put together a long term plan, none of those big projects have gotten very far.

I still write my blog posts the day before (or day of) posting them. There’s no editorial calendar. Much of what I do is just kind of played day to day or week to week, and I use the excuse of “enjoying the lifestyle” to justify that.

That being said, with more organization and planning, I wouldn’t necessarily need to cut out any of the fun.  It’s simply a matter of getting all of the pieces to play together nicely.

Hollis Carter is one of the most impressive examples of this. He’s built a 7 figure business in numerous industries, and you know why he’s done this? It’s simply so he can ski as many days of the year as possible. He’s automated everything, he does the stuff he loves, and has systems in place that allow him to hand off the stuff he doesn’t want to do.

This isn’t possible without a plan.

Why am I Sharing This?

I’ve been pretty open and vulnerable at times on this site, yet for some reason, this post has me more nervous than most similar posts I’ve shared.

I think that’s because these 7 things truly are at the epicenter of what I’m currently struggling with right now. 

Why am I posting it? A few reasons.

First, I know you’ll get some value. Most of the bloggers, authors, and entrepreneurs out there will only go surface deep with their biggest issues. They need to be seen as experts and authority figures, so usually you’ll just see the good stuff.

I don’t think your opinion of me as an expert in my space is going to change because of this, and in fact I think there’s a good chance it will only increase any respect you have for me (you know, assuming there is some haha).

But more importantly, writing this sucks. Admitting you aren’t the best at something isn’t fun. And I don’t want to write another post like this.

So the goal is to put it out there as a reminder to myself to do better. I’m by no means doing poorly, and judging by what my life looks like I think I’ve made better life choices than a lot of people – but I know it could be even better.

That’s what this is about, focusing on the things that are hard and overcoming them in order to take things to a new level.

So take a leap with me, share what your biggest mistake or struggle is in the comments, and together, as a community, we’ll continue to live lives we’ve only dreamed of.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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